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Issue 14, 2013
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Synthetic and mechanistic insight into nosylation of glycine residues

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The Fukuyama–Mitsunobu alkylation procedure is widely used to introduce alkyl substituents to amino groups in general and N-alkylation of peptides in particular. Here we have investigated the procedure in detail for N-alkylation of peptides with N-terminal glycine residues, based on the observation that standard conditions lead to substantial bis-nosylation of the glycine amino group. A systematic evaluation of this observation was carried out and it was demonstrated that for peptides with alanine, β-alanine or γ-aminobutyric acid (GABA) as N-terminal residues mono-nosylation was observed under the same conditions. Moreover, bis-nosylation was independent of the type of resin, neighboring amino acid and nature of the peptide. Calculations suggest that the reason for the bis-nosylation is the fact that the deprotonated mono-nosyl species is particularly stable in the case of the terminal Gly residue because the N residue can become closer to the SO2 unit. Finally, the mono-nosylated N-terminal glycine could be obtained by careful optimization of the procedure, adding only one equivalent of 2-nitrobenzenesulfonyl chloride.

Graphical abstract: Synthetic and mechanistic insight into nosylation of glycine residues

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Publication details

The article was received on 30 Jul 2012, accepted on 30 Jan 2013 and first published on 19 Feb 2013

Article type: Paper
DOI: 10.1039/C3OB00014A
Org. Biomol. Chem., 2013,11, 2288-2293

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    Synthetic and mechanistic insight into nosylation of glycine residues

    N. Stuhr-Hansen, T. I. Sølling and K. Strømgaard, Org. Biomol. Chem., 2013, 11, 2288
    DOI: 10.1039/C3OB00014A

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